Glycopyrrolate is a salt of quaternary ammonium cation of the muscarinic anticholinergic group. Glycopyrrolate, typically as a bromide salt, has been described for the treatment of a variety of conditions including diarrhea (U.S. Pat. No. 6,214,792 B1 and U.S. Pat. No. 5,919,760 A), urinary incontinence (U.S. Pat. No. 6,204,285 B1 and U.S. Pat. No. 6,063,808 A), and anxiety (U.S. Pat. No. 5,525,347 A). Glycopyrrolate has also been described for the treatment of hyperhidrosis in U.S. Pat. Appl. No. US 2010/0276329 A1.
Glycopyrrolate has been made available as a bromide salt or an acetate salt. The bromide salt of glycopyrrolate is sold as Rubinol®. The term “glycopyrrolate” as used in the label for Rubinol® refers to the bromide salt, also more formally referred to as glycopyrronium bromide. Glycopyrronium tosylate has been described in U.S. Pat. No. 8,558,008 B2. Glycopyrrolate used pharmaceutically is the racemic threo form.
Glycopyrronium bromide is commercially available and the synthesis has been described in U.S. Pat. No. 2,956,062 and in Finnish Pat. No. 49,713. Several routes for the production of glycopyrronium tosylate have been described in U.S. Pat. No. 8,558,008 B2.